title: A photocycloaddition/fragmentation approach toward the 3,12-dioxatricyclo[8.2.1.0(6,13)]tridecane skeleton of terpenoid natural products.
abstract: Starting from tetronate 1 (R = CH(2)OH), a short photochemical access to the 3,12-dioxatricyclo[8.2.1.0(6,13)]tridecane-skeleton 2 of briarellin and asbestinin diterpenes has been explored. In the course of these studies, a number of surprising observations were made. For example, a two-step reaction pathway to the bicyclic ketolactone 3 was discovered, which is based on tetronate 1 (R = COOMe).
authors.affiliation: Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany.
authors.forename: Jörg P
authors.initials: JP
authors.lastname: Hehn
authors.forename: Eberhardt
authors.initials: E
authors.lastname: Herdtweck
authors.forename: Thorsten
authors.initials: T
authors.lastname: Bach
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D001688:Biological Products / Q000737:chemistry*; D003500:Cyclization; D008958:Models, Molecular; D055668:Photochemical Processes; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry*
chemical_list: D000473:Alkanes; D001688:Biological Products; D013729:Terpenes; C094074:tridecane